Who is Michael Saylor? Meet the man down $1 billion in his Bitcoin investments

June 14, 2022, 6:11 PM UTC

CEO of MicroStrategy might be his day job, but when it comes to his public persona, it’s Michael Saylor’s passion for Bitcoin that stands out.

Saylor and his company MicroStrategy believe in Bitcoin so much that the company took out a $205 million loan in March, collateralized by Bitcoin, to buy more Bitcoin. 

But the rosy crypto predictions from when prices were at their peak last year look a lot different now. A widespread crypto downturn has plunged Bitcoin’s price to its lowest level since December 2020. That drop has cost MicroStrategy $1 billion in unrealized losses. And if the price of Bitcoin drops below $21,000, which it did early on Tuesday, the company could face a margin call, meaning it will be forced to put up more Bitcoin as collateral for the $205 million loan.  

Despite all this, it appears that Saylor hasn’t wavered in his Bitcoin bullishness.

On Monday, as Bitcoin fell over 13% in a single day, Saylor added “laser eyes” to his Twitter profile picture, a symbol that started in online Bitcoin communities but has since been used by high-profile figures like El Salvador’s president and U.S. Sen. Cynthia Lummis (R-Wyo.) to show their unwavering support for Bitcoin.  

On Tuesday morning, as Bitcoin continued to fall, Saylor doubled down, tweeting “stack sats and stay humble.” “Sats” refers to Bitcoin’s pseudonymous inventor, Satoshi Nakamoto, and is used as a slang term for Bitcoin. 

But who is Michael Saylor, and why has he suddenly become a figurehead of the world’s biggest cryptocurrency?  

Early life

Saylor was born in 1965 to a military family in Lincoln, Neb. He moved around a lot and finally settled in a base near Dayton during his teenage years, where he became the valedictorian of his high school and was voted most likely to succeed, according to his biography on MicroStrategy’s website

At the Massachusetts Institute of Technology, Saylor took a keen interest in aeronautics and astronautics and graduated with degrees in aeronautics and astronautics as well as science, technology, and society.

In 1989, at the age of 24, he started MicroStrategy, a business software firm that made him a billionaire during the ’90s dotcom boom. When the dotcom bubble collapsed, he lost $6 billion in a single day, but MicroStrategy stayed in business.

Saylor lost his place in the ranks of billionaires after MicroStrategy revised its financial results in 1999, but regained it last year as Bitcoin reached highs above $60,000 in November. 


In 2013, Saylor tweeted that Bitcoin’s days were numbered

But by 2020, he tweeted that he personally owned 17,732 Bitcoin, bought at an average price of $9,882 per coin. During the pandemic, Saylor said he “went down the rabbit hole” researching Bitcoin and told CoinDesk he was “wrong” for not having supported Bitcoin in its early days, when it was in the $600 range.

Saylor told CoinDesk that he started assigning Bitcoin “homework” to his MicroStrategy executives, and by the time MicroStrategy’s second-quarter earnings call came around in 2020, its chief financial officer, Phong Le, announced a new plan. The company would seek to invest $250 million of its cash in “alternative investments or assets,” which could include Bitcoin, he said. 

The company put the entire $250 million into Bitcoin, later added more, and as of March 31 of this year, MicroStrategy was the largest corporate holder of the cryptocurrency, with 129,218 Bitcoin on its balance sheet.

Saylor as a Bitcoin icon

Because of Saylor’s huge bet on Bitcoin, he has been hailed by some as a hero and condemned by others as “insane.”

He has more than 2.5 million followers on Twitter, dwarfing the 239,000 followers of crypto regulator Gary Gensler, chair of the Securities and Exchange Commission. 

Saylor has previously said he is prepared to “HODL,” a slang term for “hold on for dear life” used by crypto investors, for 100 years. Despite any downturns in the price, he has held true to his support for the cryptocurrency, despite signs that the future of Bitcoin may not be so rosy.

Michael Saylor and MicroStrategy did not immediately respond to Fortune’s request for comment.

He has argued that the people who don’t believe Bitcoin will be adopted are wrong, because it has already been widely adopted. He also believes Bitcoin won’t be regulated into obscurity, saying that the bipartisan crypto bill that Sen. Lummis and Sen. Kirsten Gillibrand (D-N.Y.) introduced last week proves that the government won’t ban the cryptocurrency. That leaves just one conclusion, Saylor said. 

“If the deniers are wrong, and if the skeptics are wrong, and it’s pretty obvious they’re both wrong at this point,” he told CNBC. “It’s not going to zero, and if it’s not going to zero it’s going to a million.”

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